Holiday rentals with a pool in Jamaica

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Jamaica

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Flat in Port Antonio

4.94 out of 5 average rating, 133 reviews

Frangipani, San San, Portland, Jamaica

Frangipani is located 5 miles east of Port Antonio, in the lush, rural, tropical subdivision of San San, beside the village of Drapers. It is within walking distance of Drapers, Frenchman's Cove and San San Beach. Port Antonio, Blue Lagoon and Boston Bay are just a few minutes drive away. The property is a self contained apartment and has a 2 lane, 1/3 Olympic length pool, (55 feet/16.6 meters). We offer discounts, 15% for one week, 20% for two weeks, 25% for three weeks, and 30% for one month.

27 Aug – 3 Sep

$121 SGD per night

Superhost

Apartment in Montego Bay

4.85 out of 5 average rating, 308 reviews

Modern apartment with a pool & amazing views!

Modern, 1BR, ground level apartment with all the modern amenities you will need for a perfect stay. Start your day having coffee on the patio gazing at the awe-inspiring coastline and turquoise lagoon. The property is part of a secure, gated development with a private community pool for guests to laze away while perfecting their tan, or hide in the shade sipping on a cold drink. You're close enough to the airport, shopping malls and nightlife - but nestled on the outskirts for quiet relaxation.

27 Sep – 4 Oct

$115 SGD per night

Guest favourite

Home in Portmore

4.91 out of 5 average rating, 137 reviews

🏝🏝HIDDEN GEMS 💎 💎 🏝🏝 Vacation Home 🏡🏞

This carefully designed house is ideal for persons looking for a cool refreshing modern and comfortable vacation stay . It is perfectly located in quiet and secure gated community Phoenix park village ,in the well developed sunshine city of portmore st catharine . It is most suitable for you because of its convenient access to all it has to offer around it ,its famous helshure beach, movie theater ,shopping malls ,clubs ,restaurants etc . it is the place for families ,couples, or just friends

13–20 Jun

$254 SGD per night

Guest favourite

Townhouse in Montego Bay

4.98 out of 5 average rating, 125 reviews

2BR Townhouse with staff, gym, pool & beach access

Escape@20 is a lovely townhome that guarantees a truly relaxing and memorable experience. A friendly housekeeper/cook is included at NO EXTRA COST!! You just need to purchase the groceries. The townhome has an open floor plan with living and dining room opening out to a covered patio and a backyard. Guests can enjoy breathtaking views of the neighboring yacht docking area, swimming pool, gazebo/bbq grill space, gym, playground for kids, 24 hour security and complimentary beach access nearby.

26 Nov – 3 Dec

$428 SGD per night

Guest favourite

Flat in Ocho Rios

4.94 out of 5 average rating, 214 reviews

Stylish Poolside Studio Near Ochi Attractions

Stylish, tropical, poolside studio. Smart home Alexa & keyless entry. Centrally located in Ocho Rios, 24-hr security, gated community of Sky Castles, 5 minute drive from popular attractions (Dunn’s River Falls, Mystic Mountain) & stores. Modern windows & porcelain floor tiles will give you a luxurious feel. Fully equipped kitchen, smart TV, Safe, walk-in shower, 1 queen bed sleeps 2 and a sofa bed sleeps 1 adult or 2 kids. Spacious patio, free parking & access to pools make this a must stay.

19–26 Oct

$135 SGD per night

Guest favourite

Flat in West End

4.94 out of 5 average rating, 140 reviews

Is This Love Ocean View Suite/ New AC

Is this love ocean view suite is located at the splashrock deep west private residences, woke up to award-winning view while watching the dolphins/ships/boats on the Caribbean Sea while drinking your coffee in the morning.We have a saltwater infinity pool overlooking the ocean sunset and sunrise are amazing from the waterfront. Enjoy a jamaican cook meals/ drink at the bar/restaurant on property. This is the hidden gem of Negril. We also have four different vacation rental units on property

24–29 May

$183 SGD per night

Guest favourite

Cottage in Cousins Cove

4.89 out of 5 average rating, 128 reviews

Ocean Cabin Private Sea Access Plunge Pool WIFI

2020 Travelers Choice Award Winner ❤️ COVID-19 Protocol Compliant Approved Listing. Charming rustic wooden cabin situated on the coral rocks just steps from the crystal clear Caribbean waters edge. Located in pristine Cousins Cove, a beautiful quiet fishing village away from the tourist traps. You can spend your days snorkeling, swimming, fishing, lazing in a hammock, chillin out in the "Cool Pool", sipping a rum (or two) playing dominoes yet all within 15 minutes of Negril's 7 mile beach.

24 Apr – 1 May

$160 SGD per night

Guest favourite

Home in Discovery Bay

4.94 out of 5 average rating, 128 reviews

Courtyard by the Bay*pvt pool*Puerto Seco bc*Solar

Escape to paradise to this beautiful built, luxurious, two-bedroom bungalow home in Discovery Bay. Discover a tropical haven with a private pool, modern comforts like FILTERED WATER(yes it's a big deal) and A1 amenities. Immerse yourself in island living, just minutes away enjoy the 5 star resort style private beach of Puerto Seco, restaurants and major attractions. Suitable for all types of travelers seeking an unforgettable vacation. Look no further BOOK NOW at Courtyard by the Bay.

7–14 Apr

$198 SGD per night

Guest favourite

Cottage in Montego Bay

4.94 out of 5 average rating, 171 reviews

Glory @ Montego Bay

Welcome to “Glory”. The cottage is situated on the grounds of our home “Victory“. We invite you to experience our concept of “Jamaican Home Living”. Glory overlooks the Sangster International Airport and the Caribbean Sea and is 5 mins from world-famous Doctors Cave Beach. We are also conveniently 5 minutes drive from the airport. We own the SeaGull @ Little Bay Country Club in Negril, and are Airbnb SuperHosts; we know how to take care of our guests. Join us for a special experience.

25 Apr – 2 May

$406 SGD per night

Guest favourite

Villa in Montego Bay

4.93 out of 5 average rating, 148 reviews

VIBES COVE enjoy your stay while getting pampered

FREE Arrival meal , the first day you arrive to vibes cove you’ll receive a complementary arrival meal by our personal chef on the property. Vibes coves villa is super Spacious and private enjoy your vacation by getting pampered. This property comes with a personal chef , Butler, and housekeeper. Enjoy V.I.P services your entire stay. Property staff stays in their helpers quarters ( not apart of the property ) only those listed on the Airbnb is allowed at the property.

13–20 Apr

$967 SGD per night

Guest favourite

Apartment in Tower Isle

4.89 out of 5 average rating, 132 reviews

2 bedroom Oceanfront condo with a pool

Kick back and relax in this calm, stylish 2 bedroom Condo on the ocean with an infinity pool. We are approx 5 minutes east of Ocho Rios and within walking distance to the Summerhouse restaurant, local jerk centre & bar, PG's Italian restaurant and a grocery store. We can host up to four guests. As we have many couples traveling we offer a discounted base rate for two guests and then each additional guest comes with an additional fee up to a maximum of four.

16–23 Sep

$289 SGD per night

Guest favourite

Bungalow in Port Antonio

4.89 out of 5 average rating, 170 reviews

Mother Nature

Mother Nature ist ein freistehendes rundes Steinhaus mit begrünter Dachterrasse. Das Haus verfügt über ein Kingsize-Bett, einem eigenem Badezimmer, Holz- und Steinterrasse, sowie großem Garten. Außerdem steht eine überdachte Außenküche zur Verfügung. Inmitten Mutter Natur kannst du die Seele baumeln lassen und deinem flow folgen. Den Vögeln und dem Wind lauschen, die Sterne beobachten, ein Sonnenbad nehmen oder im Schatten chillen. Feel free

29 Dec – 5 Jan

$148 SGD per night